this refers to a guy that appears to be attractive with a hat on but once the hat is removed you realize he is in fact balding and/or not attractive hatless, like the country singer Kenny Chesney.
I went home with that hot older guy, Matt, but when he took his hat off I could see that he was suffering from acute Chesney Syndrome.
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Term used to describe men on online dating sites who only post pictures of themselves wearing a hat, sunglasses, or both to hide the fact that they are unattractive, cross-eyed or bald.
"This guy's cute but I totally think he has Kenny Chesney Syndrome, he has a hat on in every picture"
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